How to find what doesn't feel like work!
In this episode of The Education Road, we sit down with Jacob Robinson, an attorney turned sports writer for The Athletic, whose winding journey from law school to becoming a writer covering the NFL is a testament to the power of following your curiosity and doing the reps.
Jacob’s story begins in Ontario, where a dual-degree business program at Brock University led him to Germany for two years of study abroad. That experience, he says, changed everything: living in a tiny village outside Frankfurt, learning to be resourceful, and discovering a love for exploration that would later define his career choices.
After earning degrees in both Canada and Germany, Jacob went on to law school through the University of Windsor and the University of Detroit Mercy, where he earned credentials on both sides of the border.
But it was a single Malcolm Gladwell book that changed his trajectory. Inspired by Outliers, Jacob realized that success often comes from being in the right place at the right time, and for him, that place was blockchain. While studying law, he dove deep into crypto policy, took a chance on a niche elective course, and became an early voice in decentralized law. That curiosity led to a role with the Ethereum Foundation and the creation of a popular podcast exploring crypto regulation.
Yet, the real twist came when Jacob’s side project, a fantasy football newsletter he started for fun, exploded overnight on Reddit. What began as five (forced) subscribers grew to thousands, and eventually caught the attention of The Athletic. Fast-forward to today, Jacob writes the largest NFL newsletter in the world, with over 1.4 million subscribers, delivering daily insights, humor, and analysis to football fans everywhere.
His advice to students and aspiring creators is simple: Don’t wait for permission. Start writing, start posting, start building. Whether it’s a podcast, blog, or newsletter, your work is your proof.
Jacob’s story captures what The Education Road is all about: the unpredictable, deeply human journey of learning, growing, and eventually finding work that doesn’t feel like work.